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Henry Jamison is part of the aristocratic Jamison family, a family of wealthy and influential Brahmin barons from Redding in New California who have invested heavily into the Crimson Caravan.[1] His father had pulled in some favors with the Crimson Caravan to secure Henry a position as CEO of the New Vegas branch of the Crimson Caravan as well as to get Henry out of the way for the family.[2][3] With pressure from the Jamison Family and CCC, Alice McLafferty posted Henry at the New Vegas branch.

Henry was far from suited for the job, always keeping the New Vegas branch underperforming due to his poor management skills before Alice McLafferty was sent from the Hub to straighten out the branch. Being arrogant, self-centered and irresponsible, Henry cares very little about anything besides indulging himself on gambling, drinking and prostitutes that the position can offer him and holds McLafferty in contempt for attempting to sack him.[4] With his gambling, he's built up a rather large debt with the Omertas, which he has yet to put a dent in, despite knowing fully of what the Omertas are capable of.[4]

Because of his poor management of the New Vegas branch, the Crimson Caravan wants him gone, but his family ties won't allow him to be fired. Alice McLafferty has tried urging him and his parents to make him quit or allow her to fire him, but both refuse. She is looking for someone who can help her oust him from his position. Henry can be found in Freeside gambling more at the Atomic Wrangler on the slots. For him to quit the Crimson Caravan, he wants all of his debt to the Omertas paid off in addition to a hefty severance package.[5]

↑The Courier: "I want to know more about the problem with Henry Jamison."Alice McLafferty: "The Jamisons are very wealthy ranchers back in Redding, California and significant investors in the Crimson Caravan Company. I was pressured into posting young Henry as the manager of the New Vegas branch. As you can see, he wasn't exactly cut out for the job. He was much more interested in gambling and prostitutes, and because of his family, I can't simply fire him. Henry needs to be convinced to quit, one way or another. I won't have a useless employee on the company payroll."(Alice McLafferty's dialogue)

↑The Courier: "What brought you to New Vegas?"Henry Jamison: "I wanted to be where the action is, so I got my dad to pull some strings and get me a cushy position with the Crimson Caravan. Everything was great until McLafferty came along. That old bitch is gonna hear about it from my dad, just you wait."(Henry Jamison's dialogue)

↑ 4.04.1The Courier: "I'm here to talk about ending your employment with the Crimson Caravan Company."Henry Jamison: "Fuck no. No matter what that old bitch McLafferty says, my dad said I could be in charge of the New Vegas branch. Besides, I got into a little money trouble with the Omertas. If I quit the Crimson Caravan, how am I supposed to get the money to gamble?"The Courier: "What do you know about the Omertas?"Henry Jamison: "One of the families that runs the Strip. They're a pack of cheaters, but you still don't want to fuck with them."(Henry Jamison's dialogue)

↑The Courier: "Maybe we can make a deal. What do you want from the Crimson Caravan in exchange for quitting?"Henry Jamison: "I want my debt with the Omertas paid off. And I want one of those severance package things. A big one."(Henry Jamison's dialogue)